ethyl 6H-benzo[c]chromene-2-carboxylate | 1415223-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: ethyl 6H-benzo[c]chromene-2-carboxylate
• CAS: 1415223-23-2
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: PTNAROXXBCNVSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6H-benzo[c]chromene-2-carboxylate 在 吡啶 、 叔丁基过氧化氢 、 potassium iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 以98%的产率得到ethyl 6-oxo-6H-benzo[c]chromene-2-carboxylate
  参考文献：
  名称：

  A Metal-Free Oxidation of Benzo[c]chromen to Benzo[c]chromen-6-ones by t-Butyl Hydroperoxide in the Presence of Potassium Iodide

  摘要：

  An effective and eco-friendly oxidation method for the synthesis of benzo[c]chromen-6-ones is described. The condition constitutes 6 molar ratio TBHP, catalytic KI and pyridine in acetonitrile as the solvent. Altogether, 16 structurally diverse substituted benzo[c]chromen-6-ones were prepared through this protocol from corresponding benzo[c]chromenes in excellent yields.

  DOI：

  10.3987/com-13-12760
• 作为产物：
  描述：

  ethyl 4-(benzyloxy)-3-nitrobenzoate 在 tetrafluoroboric acid 、 tin (IV) chloride pentahydrate 、 palladium diacetate 、 potassium carbonate 、 sodium nitrite 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 生成 ethyl 6H-benzo[c]chromene-2-carboxylate
  参考文献：
  名称：

  Synthesis of substituted 6H-benzo[c]chromenes: a palladium promoted ring closure of diazonium tetrafluoroborates

  摘要：

  A highly efficient palladium-catalysed phenyl diazonium tetrafluoroborate participation of C-H activation ring closure protocol has been developed. A series of 6H-benzo[c]chromenes have been synthesized by intramolecular cyclization of ortho diazonium salts tetrafluoroborate of benzyloxyphenyl (Method A), or phenoxymethyl phenyl (Method B). The transformation allows the synthesis of 6H-benzo[c]chromenes with a wide variety of functional groups and substitution patterns from simple and easily accessible precursors. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.038

文献信息

• Lewis-Acid-Promoted Arylation Reaction: Synthesis of Dihydrobenzofuran Derivatives from Aryltriazenes
  作者：Guoqing Zhao、Binjie Wang、Weijun Yang、Hongjun Ren

  DOI：10.1002/ejoc.201200902

  日期：2012.11

  A Lewis-acid-promoted approach to the synthesis of highly functionalized dihydrobenzofuran derivatives was developed. A diverse range of functional groups are tolerated in this type of reaction. The reaction mechanism investigation indicates that the highly reactive phenyl cation intermediate is probably involved in this process. The chirality of substrate is retained under the reaction conditions

  开发了一种路易斯酸促进的合成高度官能化二氢苯并呋喃衍生物的方法。在这种类型的反应中可以容忍各种各样的官能团。反应机理研究表明，高活性苯基阳离子中间体很可能参与了该过程。底物的手性在反应条件下得以保留。
• A Metal-Free Oxidation of Benzo[c]chromen to Benzo[c]chromen-6-ones by t-Butyl Hydroperoxide in the Presence of Potassium Iodide
  作者：Zhen-Ting Du、Tao Zhang、Jing Zhou、Pan Han、Ying-Meng Xu

  DOI：10.3987/com-13-12760

  日期：——

  An effective and eco-friendly oxidation method for the synthesis of benzo[c]chromen-6-ones is described. The condition constitutes 6 molar ratio TBHP, catalytic KI and pyridine in acetonitrile as the solvent. Altogether, 16 structurally diverse substituted benzo[c]chromen-6-ones were prepared through this protocol from corresponding benzo[c]chromenes in excellent yields.
• Synthesis of substituted 6H-benzo[c]chromenes: a palladium promoted ring closure of diazonium tetrafluoroborates
  作者：Jing Zhou、Liang-Zhu Huang、You-Qiang Li、Zhen-Ting Du

  DOI：10.1016/j.tetlet.2012.10.038

  日期：2012.12

  A highly efficient palladium-catalysed phenyl diazonium tetrafluoroborate participation of C-H activation ring closure protocol has been developed. A series of 6H-benzo[c]chromenes have been synthesized by intramolecular cyclization of ortho diazonium salts tetrafluoroborate of benzyloxyphenyl (Method A), or phenoxymethyl phenyl (Method B). The transformation allows the synthesis of 6H-benzo[c]chromenes with a wide variety of functional groups and substitution patterns from simple and easily accessible precursors. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.